Chloroform, CHCl3

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Chloroform is also known as Trichloromethane, Methane Trichloride, Trichloroform, Methyl Trichloride, and Formyl Trichloride. It is traditionally called ‘Chloroform’ because of its molecular similarity to Formic acid. Chloroform has a pleasant and sweet odor; it is soluble in water and able to be mixed with oils, ethanol, ether, and other organic solvents. Chloroform becomes unstable when it is exposed to any combination of air, light, and heat. When Chloroform is heated until it decomposes, it gives off toxic fumes of hydrochloric acid and other chlorinated compounds.

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Other Properties of Chloroform:

Specific Gravity: 1.50
Vapour Density: 4.1
CASR Number: 67-66-3



Appearance
Chloroform is a clear and colorless liquid. It is reflective, non-flammable, and highly volitile.
Chloroform has a sweet odor that is not at all irritating. However, if inhaled, it could be deadly.

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The Discovery of Chloroform
Samuel Guthrie, American physician, discovered chloroform in July 1831. His process involved mixing whiskey with chlorinated lime that formed an alcoholic solution of Chloroform. When first made, it was known as "Guthrie's Sweet Whiskey." Not long after Gutherie's discovery, Eugene Soubeiran and Justus von Leibig discovered it independently. Later, in 1834, Jean-Baptiste Dumas named and characterized it. In 1847, Marie-Jean-Pierre Flourens also played a part by noting and characterizing all of the anesthetic properties of Chloroform.

Producing Chloroform
The main way that Chloroform is made today is a complicated process of the action of iron and acid on carbon tetrachloride. Chloroform was first produced by a reaction called the haloform reaction. The haloform reaction is a reaction of ethanol or acetone with sodium hypochlorite or calcium hypochlorite.The Chloroform is then removed from the formate salts or acetate salts through distillation. The haloform reaction is no longer used to produce Chloroform.


How Obtained
“The chemical formula of Chloroform is ChCl3. It is obtained by synthesis, which is an entirely chemical process. Chlorine is made to pass through alcohol at a boil. What follows is the chlorination of the methyl group to an aldehyde along with oxidation of the alcohol group, resulting in the formation of trichloro-acetaldehyde or chloral. Now the chloral is applied with caustic alkali, which results in the fission of C-C linkages. The result is Chloroform and formate.

A do-it-yourself procedure involving bleach, acetone and ice is also possible to obtain Chloroform. But this carries several risks. Chloroform is not manufactured for villains to subdue innocent damsels, but rather has various industrial uses. It is no longer manufactured in abundance as other cheaper and less dangerous substitutes have been discovered.”
: http://www.blurtit.com/q883306.html

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Explanation of Structure


Type of bonding:
The bonds of Chloroform form a tetrahedral shape. The atoms form 109.5º bond angles. Chloroform is made up of one hydrogen and three chlorine atoms bonded to a carbon.
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Natural Abundance

“McCulloch (2003) reported an approximate global chloroform flux of 660 000 tonnes per year and estimated that about 90% of these emissions were natural in origin.”

“approximate global chloroform flux of 660 000 tonnes per year”

http://www.inchem.org/documents/cicads/cicads/cicad58.htm

After forming in small amounts biogenically in spruce forest soil by (12 µg/m2 per day), Chloroform then evaporates and slowly breaks down into other toxic chemicals such as phosgene and hydrogen chloride. Chloroform dissolves in water and then evaporates to air and reacts with photochemically generated hydroxyl radicals. The products are dichloromethane, phosgene, formyl chloride, carbon monoxide, carbon dioxide, and hydrogen chloride. Most Chloroform ends up in the air. Only a small percentage of Chloroform ultimately ends up in water.

Found

“organic-rich spruce forest soil” “biogenic formation”
http://www.inchem.org/documents/cicads/cicads/cicad58.htm



The Medicinal Use of Chloroformchloform.jpg:

Sir James Young Simpson discovered the medicinal use of Chloroform. It is used as a general anesthetic. Anesthetics make the user lose consciousness long enough to perform a painless surgery. A patient is usually taken to the third stage of Chloroform inhalation when having a surgery performed on them. Ether was the first anesthetic and the most common until Chloroform's medical use was discovered.

The 5 Stages of effects when Chloroform is inhaled.

  • Conscious but insensible
  • Lethargic state – could feel some pain
  • Cannot feel any pain
  • Muscles completely relaxed
  • Paralysis of the chest muscles (often fatal)


Additional Uses of Chloroform

Today, Chloroform is used mainly in the production of fluorocarbon-22, a refrigerant, and in the production of fluoropolymers. Chloroform is additionally used as a solvent in many different ways, one being in the extraction and purification of various antibiotics, alkaloids, vitamins, and flavors. It is also used as a solvent in photography and dry cleaning. Its use as an anesthetic has been discontinued due to many sudden deaths from using it. Chloroform is commonly used in the production of plastics (especially vinyl chloride). Chloroform can be used as an extraction solvent for oils, fats, greases, waxes, rubber, gutta-percha, lacquers, resins, gums, and adhesives. Chloroform is an industrial solvent in the extraction and purification for certain alkaloids, antibiotics, flavors, and vitamins. Chloroform is used in fire extinguishers to lower freezing temperatures of carbon tetrachloride. However, Chloroform is being replaced by less dangerous solvents.

Disadvantages of Chloroform

Even though Chloroform has done many things, there are also some disadvantages to it. First, we have found in the medical world that it is easy to overdose on it. There has been too many deaths from the use of this product. Additionally, the use of Chloroform can lead to liver damage and it has been found to be a possible cause of cancer.


NPI Rank

The NPI (National Pollutant Inventory) ranked 400 substances. The NPI Rank for Chloroform is 66. Chloroform's total hazard score is 2.5. This number is out of 3. The ranking is based on health and environmental hazards. The number also reflects human and environmental exposure to Chloroform. On a health hazard rating of 0 - 3, Chloroform is a 1.5. A 3 represents a very high hazard to health. 2 represents a medium hazard. 1 is harmful to health. On an environmental rating of 0 - 3, Chloroform registers 1.0. A 3 represents a very high hazard to the environment and a 0 a negligible hazard. This scale is based on a compound's toxic nature. The scale also includes the measure of a compound's ability to remain active in the environment as well as if it accumulates in living organisms.

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Chloroform is unsafe, but people don't realize that they come in contact with it every day. It can be found in a person's food, water, and air.



References:


http://www.general-anaesthesia.com/images/chloroform.htm
This website is filled with general information about chloroform, including the history, chemical properties, and real life situations involving chloroform.
http://www.chm.bris.ac.uk/motm/chloroform/chloroformv.htm
This website includes general information about chloroform. It also goes in depth with its history and different pieces of data that deal with the compound.
http://www.asmalldoseof.org/historyoftox/1800s/chloform.jpg
This is a link to one of the pictures used for our web page.
http://www.inchem.org/documents/cicads/cicads/cicad58.htm
This is a website made up of "the collective views of an international group of experts."
http://mutuslab.cs.uwindsor.ca/macdonald/images/SymmetryPictures/Symmetry.htm
chime image
http://www.blurtit.com/q883306.htmlTerms
This website provides a short description on how chloroform is made.
http://www.iephb.nw.ru/~spirov/hazard/chloroform.html
This website provides a picture, and detailed information about the use of chloroform, the properties of chloroform, and information of the effects of exposure to chloroform.
http://www.npi.gov.au/database/substance-info/profiles/23.html#naturalsources
This site focuses on chloroform's NPI rating. It also provides information about chloroform's chemical properties.
http://www.wellesley.edu/Chemistry/Flick/molecules/Chcl3.html
This website is the source for the chloroform chime image.